EP3938341A1 - Hexylamine salts and methods of using hexylamine - Google Patents
Hexylamine salts and methods of using hexylamineInfo
- Publication number
- EP3938341A1 EP3938341A1 EP20790966.4A EP20790966A EP3938341A1 EP 3938341 A1 EP3938341 A1 EP 3938341A1 EP 20790966 A EP20790966 A EP 20790966A EP 3938341 A1 EP3938341 A1 EP 3938341A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hexylamine
- salt
- human subject
- human
- effective amount
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 238000000034 method Methods 0.000 title claims abstract description 65
- 150000003839 salts Chemical class 0.000 claims abstract description 114
- 239000000203 mixture Substances 0.000 claims abstract description 48
- VOWJWRCRVBHXLD-UHFFFAOYSA-N C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(CCCCC)N(CCCCCC)CCCCCC Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(CCCCC)N(CCCCCC)CCCCCC VOWJWRCRVBHXLD-UHFFFAOYSA-N 0.000 claims abstract description 46
- 230000001965 increasing effect Effects 0.000 claims abstract description 38
- SOKZHKVMIMOJPL-UHFFFAOYSA-N C(CCCCC)N.C(CCC(=O)O)(=O)O Chemical class C(CCCCC)N.C(CCC(=O)O)(=O)O SOKZHKVMIMOJPL-UHFFFAOYSA-N 0.000 claims abstract description 31
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
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- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
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- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
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- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C59/265—Citric acid
Definitions
- Hexylamine also known as n-hexylamine, n-hexyl -ammonium, and 1-aminohexane, is a chemical compound with molecular formula CH 3 (CH 2 )5NH2 and the structure of Formula (I).
- Hexylamine is a colorless liquid and is one of the isomeric amines of hexane. At standard temperature and pressure, hexylamine is soluble in almost all organic solvents. It has the ammonia/bleach odor common to amines, which has also been reported as smelling“fishy.” It is found in trace amounts (less than 1 ppm) in some foods, such as beer, wine, camembert cheese, and milk (Maga et ak, Amines in foods). However, it is not known whether a human would benefit from hexylamine supplementation.
- the disclosure relates to salts of hexylamine, for example, hexylamine succinate and tri-hexylamine citrate and their method of production.
- the method of producing hexylamine succinate comprises gradually mixing hexylamine into succinic acid to produce a solution comprising hexylamine succinate.
- the temperature of the solution comprising hexylamine succinate is at a temperature lower than 131°C.
- the method of producing tri- hexylamine citrate comprises combining a hexylamine and citric acid at a molar ratio of 3 mol hexylamine to 1 mol citric acid.
- Citric acid is first dissolved in a suitable solvent to produce a saturated solution of citric acid. Hexylamine is then added drop by drop to the saturated solution of citric acid to produce a mixture containing a precipitate. During the addition of hexylamine, the saturated solution of citric acid is continually stirred. In some method of producing tri- hexylamine citrate, the method further comprises stirring the mixture containing the precipitate for at least 15 minutes after all of the hexylamine is added to the saturated solution of citric acid. Afterwards, the precipitate is filtered out of the mixture and dried to collect the tri-hexylamine citrate.
- the solvent for producing the saturated solution of citric acid is acetone. Accordingly, the saturated solution of citric acid is preferably prepared at a temperature of no higher than 70°C, for example at room temperature.
- compositions comprising a salt of hexylamine and a dietary ingredient, a food additive or a pharmaceutically acceptable additive.
- the salt of hexylamine is selected from the group consisting of: the hydrochloride, the nitrate, the sulfate, the citrate, the malate, the maleate, the succinate, the fumarate, and the acetate.
- the salt of hexylamine in the composition is hexylamine succinate or even more preferably tri-hexylamine citrate.
- the disclosure relates methods of reducing appetite in a human subject, treating obesity in a human subject, preventing obesity in a human subject, preventing weight gain in a human subject, increasing fat loss in a human subject, treating an overweight human subject, increasing athletic performance in a human subject, increasing endurance in a human subject, increasing muscle strength in a human subject, improving cognitive function in a human subject, treating ADHD in a human subject, increasing sweating in a human subject, reducing reaction time of a human subject, and increasing psychomotor vigilance of a human subject.
- the methods comprise administering to the human subject a pharmaceutically effective amount of hexylamine or a suitable salt.
- the pharmaceutically effective dose provides between 5 mg and 5000 mg hexylamine, for example, between 100 mg and 800 mg hexylamine. In some aspects, the pharmaceutically effective dose is administered to the human subject two times a day. In other aspects, the pharmaceutically effective dose is administered to the human subject three times a day. In certain implementations, the human subject is administered hexylamine succinate or tri-hexylamine citrate.
- Fig. 1 depicts a comparison of hexylamine succinate and hexylamine tartrate after being left exposed to air for a period of a month.
- Hexylamine succinate top beaker
- hexylamine tartrate bottom beaker
- Fig. 2 depicts a comparison of monohexylamine citrate and tri-hexylamine citrate after being left exposure to air for one day. Monohexylamine citrate (left) hardened into a solid mass while tri-hexylamine citrate (right) suffered from some caking.
- Fig. 3 depicts a time course of tri-hexylamine citrate in water.
- One gram of tri- hexylamine citrate was scattered over 100 ml water at room temperature (left). About one minute after, all of the tri-hexylamine citrate was dissolved (right).
- room temperature refers to a temperature range of 20 to 25°C with excursions between 15 to 30°C, provided that the mean kinetic temperature does not exceed 25°C. In some aspects,“room temperature” refers to a temperature range of 15 to 25°C.
- saturated solution refers to a solution in which the maximum amount of solute has been dissolved. Accordingly, a saturated solution of citric acid is a solution in which the maximum amount of citric acid is dissolved in a solvent.
- cognitive function encompasses all aspects of conscious brain function. As such, cognitive function includes learning and memory, planning, attention, problem-solving, and sensory perception.
- dietary supplement refers to an addition to the human diet, which is not a natural or conventional food.
- the term“effective amount” refers to an amount that is effective for a specific patient. In some aspects, the term“effective amount” refers to a pharmaceutically effective amount, which an amount that is effective in a clinical trial.
- suitable for human consumption refers to a compound or composition that is generally safe, non-toxic, and can be used as in medication, dietary supplement or even food.
- the amount refers to the amount of the free base that can yield from the salt after dissociation.
- hexylamine succinate is 219.183 Dalton, of which 46.14% is hexylamine.
- tri -hexyl amine citrate 495.694 Dalton
- the theoretical percentage of hexylamine in the salt would be about 61%.
- Hexylamine by itself is a foul-smelling liquid at room temperature. It is caustic on contact with the skin or tongue, which could explain why no one sought to increase intake of hexylamine by ingestion of the compound.
- a salt of hexylamine that has favorable organoleptic, pharmacokinetic, and pharmacotechnical properties for use in a dietary supplement or composition for human ingestion, a variety of hexylamine salts, including the hydrochloride, the nitrate, the sulfate, the citrate, the malate, the maleate, the succinate, the fumarate, and the acetate, were synthesized.
- hexylamine succinate and tri- hexylamine citrate were the best candidates for use in a a dietary supplement or composition for human ingestion.
- the succinate was the easiest to produce.
- the disclosure relates to the synthesis of hexylamine succinate.
- the method of producing hexylamine succinate required only direct addition of hexylamine to succinic acid at equimolar parts without the need for any additional solvents.
- hexylamine is gradually mixed into succinic acid to produce a solution comprising hexylamine succinate so that the temperature of the solution comprising hexylamine succinate does not exceed 131°C.
- the solution comprising hexylamine succinate is maintained at a temperature of less than 70°C.
- the resultant succinate salt can be immediately formed into powder, unlike the sulfate or fumarate salts, which require grinding in order to produce a fine powder.
- grinding hexylamine salts could results in serious health toxicity and undesired environmental modifications (for example, unpleasant odor).
- the succinate lacked any offending smell.
- the succinate also tasted the best out of the salts synthesized.
- the succinate salt is non- hydroscopic. Therefore, the novel salt hexylamine succinate is a preferred choice with the unexpected properties of improved taste, good solubility and dissolution rate, improved stability, reduced hygroscopicity, ease of formulation and excellent powdered characteristics.
- Tri-hexylamine citrate is a very stable salt with the additional benefit of carrying a lot of hexylamine by weight compared to other monohexylamine salts.
- hexylamine is slowly added to a saturated solution of citric acid in a ratio of about 3 mol hexylamine to about 1 mol citric acid.
- the hexylamine is added drop by drop into the saturated solution of citric acid.
- the saturated solution of citric acid is continuously stirred. Once all of the hexylamine has been added to the saturated solution of citric acid, the mixture is stirred for at least another 15 minutes. The white precipitated formed in the mixture is then filtered out and dried to collect the produced tri-hexylamine citrate.
- the solvent for making the solution of citric acid must be one in which citric acid and hexylamine are soluble with no chemical reactions taking place.
- the solvent is not aqueous.
- the solvent is anhydrous.
- the solvent is acetone to make a saturated solution of citric acid in acetone.
- the saturated solution of citric acid in acetone is prepared by adding 20 g citric acid to 1000 ml acetone. The amount of citric acid dissolvable in acetone is higher at higher temperatures.
- acetone evaporates at around 80°C and is a fire and health hazard, so the preparation of the saturated solution of citric acid in acetone should not use acetone heated to a temperature higher than 70°C, preferably no higher than 40°C, for example, at room temperature.
- Amylamine the closest chemical entity to propylamine, has also been described as a compound that can reduce cardiac function, reduce heartbeat, and reduce body temperature, which are characteristics of a compound with a probable anti-stimulatory effect (Page 1999 of King’s American Dispensatory (Felter and Lloyd eds., 1909), The Ohio Valley Company, Cincinnati). These early observations about amylamine were confirmed: administration of doses starting at 300 mg would among other effects produce reduction in heart rate and a drop in body temperature. Accordingly, compound having similar structure to hexylamine were expected to reduce alertness and cognitive function due to their sedative effects (from de facto slowdown of brain activity).
- Example 4 the administration of hexylamine increased body temperature, heart rate, systolic blood pressure, and diastolic blood pressure. The subjects also reported increased sweating. In addition, the subjects reported experiencing positive psychological and mental changes, for example, reduced appetite, increased mental acuity, and increased memory recollection.
- Example 6 further demonstrates administration of hexylamine improves cognitive function, though no significant changes in heart rate, systolic blood pressure, and diastolic blood pressure were observed in the larger study.
- Example 4 and Example 7 administration of hexylamine caused physical performance changes, for example, reduction of fatigue, increase in athletic performance, increase in endurance, and increase in strength.
- the disclosure relates to the use of hexylamine for reducing appetite in a human subject, treating obesity in a human subject, preventing obesity in a human subject, preventing weight gain in a human subject, increasing fat loss in a human subject, treating an overweight human subject, increasing athletic performance in a human subject, increasing endurance in a human subject, increasing muscle strength in a human subject, improving cognitive function in a human subject, treating ADHD in a human subject, increasing sweating in a human subject, reducing reaction time of a human subject, increasing psychomotor vigilance of a human subject, enhancing memory in a human subject, increasing central nervous system activity in a human subject, and enhancing alertness, attention, concentration, and/or memory in a human subject.
- the methods comprise administering to a human subject in need thereof a pharmaceutically effective amount of hexylamine or a salt thereof.
- the pharmaceutically effective amount of hexylamine is between about 5 mg and about 5000 mg per day, which can be taken in multiple doses during the day.
- the pharmaceutically effective amount of hexylamine in a single dose is between 50 mg and 1000 mg, between 75 mg and 750 mg, or between 100 mg and 750 mg.
- a pharmaceutically effective amount of hexylamine in a single dose is between about 100 mg and about 600 mg.
- the disclosure also relates to compositions comprising hexylamine or a salt thereof.
- the disclosure relates to a stimulatory composition, a nootropic composition for boosting cognitive function, a pre-workout composition, or a composition for aiding fat loss, the compositions comprising an effective amount of hexylamine or a salt thereof.
- the effective amount of hexylamine is between about 5 mg and about 5000 mg per day, for example, between 50 mg and 1000 mg, between 75 mg and 750 mg, between 100 mg and 750 mg, about 100 mg, about 250 mg, about 500 mg, about 600 mg, or about 750 mg.
- the compositions are topical or suitable for human ingestion.
- compositions further comprises one or more additional ingredient, for example, flavoring agents, colorants, viscosity modifiers, viscosity improvers, preservatives, fragrances, flow modifiers, chelating agents, surfactants (including anionic, cationic or nonionic surfactants), amino acids (including their derivatives or salts thereof), vitamins, minerals, essential fatty acids, enzymes, co-enzymes, mono-glycerides, di-glycerides, tri-glyceride ester oils emulsifiers, hydrolyzed proteins, whey protein, stabilizers, anti-oxidants, anti-microbials, benzoates, alcohols, esters of para- hydroxybenzoic acid, propionates, herbal extracts or constiuents thereof, fruit extracts or constituents thereof, vegetable extracts or constituents thereof, herbal oils, herbal infusions, herb powder, fruit powder, vegetable powder, tea extracts or constituent thereof, and/or elemental metals (for example, elemental zinc).
- additional ingredient for example,
- the stimulatory composition comprises an effective amount of hexylamine or a salt thereof and an effective amount of a stimulant selected from the group consisting of: yohimbine, ephedrine, ephedra sinica extracts, 1,3-dimethylamylamine, tyramine, n-methyl tyramine, synephrine, methyl-synephrine, theophylline, theobromine, theacrine, N,N- dimethyl phenethyl amine, 1,3-dimethylbutylamine, oxilofrine, 1,5-dimethylhexylamine, N,alpha-diethylphenylethylamine, liberine, methylliberine, methyl caffeine, and pharmaceutically acceptable salts, esters, or amides thereof.
- the effective amounts of hexylamine or a salt thereof and of the stimulant are pharmaceutically effective amounts.
- the nootropic composition comprises an effective amount of hexylamine or a salt thereof and an additional nootropic ingredient selected from the group consisting of: 5-HTP (5-hydroxytryptophan); carnitine or a salt, ester, or amide suitable for human ingestion thereof; acetyl -L-carni tine or a salt, ester, or amide suitable for human ingestion thereof; propionyl-L-carnitine or a salt, ester, or amide suitable for human ingestion thereof; alpha lipoic acid; alpha-GPC; aniracetam; piracetam; phenylpiracetam; apoaequorin; artichoke; ashwagandha; astaxanthin; Bacopa monnieri cat's claw; catuaba, cannabidiol (CBD); Celastris paniculatus ; centrophenoxine: citicoline; Clitoria ternatea ; coluracetam; Convolvulus plu
- the nootropic composition is more effective than the use of the additional nootropic ingredient alone. Accordingly, the nootropic composition may comprise less amount of the additional nootropic ingredient than the amount of the additional nootropic ingredient needed to have a positive nootropic effect. In some aspects, the effective amount of hexylamine or a salt thereof is a pharmaceutically effective amount.
- the disclosure also relates to the use of hexylamine to prevent side effects of caffeine ingestion, for example, caffeine- induced jitters (feelings of extreme nervousness usually accompanied by trembling of the extremities) or a caffeine crash (feeling of drowsiness and lack of energy that develops hours after caffeine intake).
- the method comprises coadministering to the human subject an effective amount of caffeine and an effective amount of hexylamine or a salt thereof.
- the disclosure also relates to a composition for enhancing memory and/or increasing central nervous system activity comprising an effective amount of hexylamine or a salt thereof and an effective amount of caffeine.
- the effective amount of hexylamine or a salt thereof provides between about 5 mg and about 5000 mg hexylamine per day, for example, between 50 mg and 1000 mg, between 75 mg and 750 mg, between 100 mg and 750 mg, about 100 mg, about 250 mg, about 500 mg, about 600 mg, or about 750 mg.
- the effective amount of caffeine is between 50 mg and 600 mg, for example, between 50 mg and 500 mg, between 100 mg and 400 mg, between 100 mg and 300 mg, about 50 mg, about 100 mg, about 150 mg, about 300 mg, about 400 mg, about 500 mg, or about 600 mg.
- salts of hexylamine are prepared by mixing liquid hexylamine into the desired acid.
- salts of hexylamine are prepared by mixing hexylamine and an acid in an appropriate solvent, such as ethanol. The salt is then separated from the solution by either recrystallization, evaporation of the solvent, or other similar methods of collecting the salt product
- Hexylamine succinate (structure shown in Formula II) was effectively synthesized by pouring an equimolar amount of hexylamine into succinic acid powder while continuously stirring in an ice bath so that the temperature of the salt solution would be over 131°C. Over the course of one week of storage, the succinate was surprisingly found to be non-hygroscopic and gain less than 1% water in the atmosphere.
- Hexylamine succinate and hexylamine tartrate were left exposed for a period of a month. As can be seen on the picture, hexylamine succinate (top beaker) remained a fine powder and gained little moisture. On the other hand, hexylamine tartrate (bottom beaker) absorbed moisture from the atmosphere and suffered from extensive caking.
- a male human subject 38 years old, 250 lbs was administered a single 100 mg hexylamine succinate, and his tolerance to the salt was record.
- the daily dose was increased increased daily to determine the highest daily dose that could be tolerance by the subject.
- a daily dose of 800 mg and higher the subject reported side effects such as feelings of discomfort.
- Hexylamine was generally well-tolerated. None of the subjects experienced any of the toxic side effects described for too much exposure hexylamine, which include, burning sensation, abdominal pain, shock, or collapse. However, the effectiveness would diminish with doses less than 100 mg.
- the salt form of hexylamine plays a major role in the stability and possession of activity (or lack thereof) of hexylamine.
- Some salt forms like the fumarate possessed little to no activity, accompanied by issues with their stability, solubility, dissolution rate and hygroscopicity.
- Other forms, like the nitrate salt were liquid at standard room temperature and pressure, which made those forms unsuitable for most formulations. In fact, the nitrate salt is very irritating on contact with the skin or mouth.
- Applicant developed a novel, non-conventional hexylamine salt, tri -hexylamine citrate (C24H53N3O7 or 3(C 6 H I6 N hGUsO- , calculated molar mass of 495.69 g/mol), which possesses all the desirable properties for a safe and effective hexylamine supplement: fast dissolution rate, superior solubility, non-toxic, and stable at standard temperature and pressure.
- Tri-hexylamine citrate has the following molecular structure: [0044] Whereas the calculated theoretical percentage of citric acid in the salt would be -39%, the certificate of analyzed for the synthesized hexylamine salt reported a citric acid was 43%. This difference could be attributed to a variety of environmental factors, for example, moisture in the tested sample or overabundance of one of the reactants. Direct combination of citric acid and hexylamine does not form tri-hexylamine citrate. Instead, the process forms mono-hexyl amine citrate, as evidenced by the salt having triple the density than hexylamine.
- mono-hexylamine citrate sinks to the bottom.
- Mono-hexylamine citrate also has a much slower dissolution rate in water when compared with tri-hexylamine citrate.
- mono-hexylamine citrate has the consistency of a paste, which makes it unsuitable for formulation or for further reactions. The consistency also indicates mono-hexylamine citrate is highly hygroscopic.
- hexylamine should be slowly added to a saturated solution of citric acid in acetone.
- the saturated solution of citric acid in acetone is prepared by adding 20 g citric acid to 1000 ml acetone.
- the amount of citric acid dissolvable in acetone is higher with higher temperatures.
- acetone evaporates at around 80°C and is a fire and health hazard, so the preparation of the saturated solution of citric acid in acetone should not use acetone heated to a temperature higher than 70°C, preferably no higher than 40°C.
- the blood pressure of the subjects was measured, and the subjects completed a questionnaire to describe their mood before the subjects were orally administered either placebo dose (dextrose capsule) or 1000 mg tri-hexylamine citrate (containing about 600 mg hexylamine). If the subject received the placebo dose on day one, then the subject received tri-hexylamine citrate on day two, and vice versa. The administration of placebo or tri- hexylamine citrate was random, and both the subject and the person administering the test were blinded.
- the mood assessment involves the subjects self scoring on a scale of 1-10, with ten being the greatest, regarding whether the extent they feel sleepy, groggy, energetic, attentive, focused, tense, alert, nervous, happy, and sad.
- the blood pressure of the subjects was measured 15 minutes after administration of the placebo dose or tri-hexylamine citrate, and the subjects completed a questionnaire to describe their mood a second time. Afterwards, the subjects completed a psychomotor vigilance test via the sleep-2-Peak mobile application (Brunet et ah,“Validation of sleep-2-Peak: A smartphone application that can detect fatigue-related changes in reaction times during sleep deprivation,” Behav Res , 2017, 49: 1460-1469), Iowa trail making test, and the digit symbol substitution test (DSST) to assess their cognitive function. After the completion of the tests, the blood pressure of the subjects was measured were measured a third time, and the subjects completed a questionnaire to describe their mood a third time. At 50 minutes after administration, the blood pressure of the subjects was measured were measured a fourth time, and the subjects completed a questionnaire to describe their mood a fourth time.
- the sleep-2-Peak mobile application Brunauer et ah,“Validation of sleep-2-Peak
- map A The Iowa trail making test assesses visual attention and task switching.
- map B the subject is to draw lines to connect circled numbers and letters in an alternating numeric and alphabetic sequence (1-A-2-B-%) as rapidly as possible. Accordingly, map A assesses cognitive processing speed, while map B asses executive function. If the subject makes an error, it was immediately pointed it out and the subject was allowed correct it. Accordingly, errors affect the score only in that the correction of errors is included in the completion time for the task.
- the DSST is a cognitive function test designed to understand human associative learning.
- the subjects receive a single sheet of paper that requires them to match symbols to numbers according to a key located on the top of the page.
- the subjects copy the symbol into spaces below a row of numbers.
- the number of correct symbols within the allowed time usually 90 to 120 seconds, constitutes the score.
- a good performance on the DSST requires intact motor speed, attention, and visuoperceptual functions, including scanning and basic manual dexterity.
- the DSST is sensitive to impairments and improvement in processing speed, executive functioning, and working memory.
- Pre-workout powder comprising hexylamine to increase athletic performance (per dose):
- Nootropic formulation for boosting cognitive function 1000 mg hexylamine (in the form of tri -hexylamine citrate)
Abstract
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